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Volumn 50, Issue 37, 2011, Pages 8660-8664

Highly regio- and stereoselective synthesis of multialkylated olefins through carbozirconation of alkynylboronates and sequential Negishi and Suzuki-Miyaura coupling reactions

Author keywords

cross coupling; Negishi coupling; palladium; Suzuki Miyaura coupling; zirconacycles

Indexed keywords

C-C BOND FORMATION; CARBOMETALATION; CROSS-COUPLINGS; ELECTROPHILES; NEGISHI COUPLING; STEREOSELECTIVE SYNTHESIS; SUZUKI-MIYAURA COUPLING; SUZUKI-MIYAURA COUPLING REACTION; SUZUKI-MIYAURA CROSS-COUPLING REACTION; ZIRCONACYCLES;

EID: 80052474735     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103601     Document Type: Article
Times cited : (53)

References (68)
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    • in, Chapter 2 (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York
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    • 2]/2 EtMgBr in the absence of an ethylene atmosphere, the yields of the desired alkenylboronates 2 were lower. For example, for 2 a, 81 % vs. 56 % yield
    • 2]/2 EtMgBr in the absence of an ethylene atmosphere, the yields of the desired alkenylboronates 2 were lower. For example, for 2 a, 81 % vs. 56 % yield.
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    • 2 (5 mol %) was used as a catalyst with various phosphine ligands; dppe (17 %), dppp (52 %), Ruphos (53 %), Xphos (53 %), and Xantphos (38 %)
    • 2 (5 mol %) was used as a catalyst with various phosphine ligands; dppe (17 %), dppp (52 %), Ruphos (53 %), Xphos (53 %), and Xantphos (38 %).
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    • 3 (7:1; 65 %)
    • 3 (7:1; 65 %).
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    • It has been reported that 1,1-borylzinc reagents can be with 1-iodo-1-octene under Negishi conditions, in which the boron functionalities are compatible
    • It has been reported that 1,1-borylzinc reagents can be with 1-iodo-1-octene under Negishi conditions, in which the boron functionalities are compatible, see:, J. R. Waas, A. R. Sidduri, P. Knochel, Tetrahedron Lett. 1992, 33, 3717-3720.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3717-3720
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    • This compound has been proposed as a propylene tetramer, but no spectroscopic data was available: CAS-number [303962-00-7]. See
    • This compound has been proposed as a propylene tetramer, but no spectroscopic data was available: CAS-number [303962-00-7]. See:, Y. T. Vigranenko, Kinet. Catal. 2000, 41, 451-456.
    • (2000) Kinet. Catal. , vol.41 , pp. 451-456
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    • 1H} NMR spectra. However, their expanded spectra in a range of 29-30 ppm indicates that there is a slight difference between the alkyl signals. See the Supporting information
    • 1H} NMR spectra. However, their expanded spectra in a range of 29-30 ppm indicates that there is a slight difference between the alkyl signals. See the Supporting information.
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    • A. A. Quntar, A. Botvinik, A
    • A. A. Quntar, A. Botvinik, A.
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    • A one-pot palladium-catalyzed methylation from C through transmetalation to copper gave a lower yield of product
    • A one-pot palladium-catalyzed methylation from C through transmetalation to copper gave a lower yield of product.
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    • The configuration of 12 was unambiguously confirmed by an NOESY measurement. See the Supporting Information
    • The configuration of 12 was unambiguously confirmed by an NOESY measurement. See the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.